Recent investigations in synthesis of α-hydroxycarboxylic acids by reductive carboxylation of aldehydes with CO2 (microreview)

Document Type : Review Article

Authors

1 College of Food Sciences, Al-Qasim Green University, Babylon, Iraq

2 National University of Science and Technology, Dhi Qar, Iraq

3 Medical Technical College, Al-Farahidi University, Iraq

4 Department of Pharmacy, Al-Noor University College, Nineveh, Iraq

5 Department of Pharmacy, Al-Zahrawi University College, Karbala, Iraq

6 Department of Chemistry, Payame Noor University, P.O. Box 19395-3697 Tehran, Iran

Abstract
Carbon dioxide (CO2) is a plentiful, nontoxic, nonflammable, renewable C1 feedstock and the major component of greenhouse gases, thereby the research for sustainable and efficient conversion of this waste gas into valuable chemicals has received great attention in recent years. The catalytic reaction between aldehydes and CO2 is a novel and attractive pathway for CO2-utilization as it can lead to the formation of highly important α-hydroxycarboxylic acids with ideal atom economy. This review discusses the advancements made within this research topic with the hope of promoting future research in the field of CO2-utilization.

Graphical Abstract

Recent investigations in synthesis of α-hydroxycarboxylic acids by reductive carboxylation of aldehydes with CO2 (microreview)

Keywords

Subjects


[1] IPCC (2022) Climate Change 2022: Mitigation of Climate Change. P.R. Shukla, J. Skea, R. Slade, A. Al Khourdajie, R. van Diemen, D. McCollum, M. Pathak, S. Some, P. Vyas, R. Fradera, M. Belkacemi, A. Hasija, G. Lisboa, S. Luz, J. Malley. Cambridge University Press, Cambridge, United Kingdom and New York, NY, USA.
[2] G. Yuan, C. Qi, W. Wu, H. Jiang, Recent advances in organic synthesis with CO2 as C1 synthon. Curr. Opin. Green Sustain. Chem., 3 (2017) 22-27.
[3] Y. Shi, B.W. Pan, Y. Zhou, J. Zhou, Y.L. Liu, F. Zhou, Catalytic enantioselective synthesis using carbon dioxide as a C1 synthon. Org. Biomol. Chem., 18 (2020) 8597-8619.
[4] B.B. Asare Bediako, Q. Qian, B. Han, Synthesis of C2+ Chemicals from CO2 and H2 via C–C bond formation. Acc. Chem. Res., 54 (2021) 2467-2476.
[5] G. Naik, N. Sarki, V. Goyal, A. Narani, K. Natte, Recent trends in upgrading of CO2 as a C1 reactant in N‐and C‐methylation reactions. Asian J. Org. Chem., 11 (2022) 202200270.
[6] E. Vessally, K. Didehban, M. Babazadeh, A. Hosseinian, L. Edjlali, Chemical fixation of CO2 with aniline derivatives: A new avenue to the synthesis of functionalized azole compounds (A review). J. CO2 Util., 21 (2017) 480-490.
[7] S. Arshadi, E. Vessally, M. Sobati, A. Hosseinian, A. Bekhradnia, Chemical fixation of CO2 to N-propargylamines: A straightforward route to 2-oxazolidinones. J. CO2 Util., 19 (2017) 120-129.
[8] R. Zhang, D. Hu, Y. Zhou, C. Ge, H. Liu, W. Fan, L. Li, B. Chen, Y. Cheng, Y. Chen, W. Zhang, Tuning ionic liquid-based catalysts for CO2 conversion into quinazoline-2, 4 (1H, 3H)-diones. Molecules, 28 (2023) 1024.
[9] S. Bierbaumer, M. Nattermann, L. Schulz, R. Zschoche, T.J. Erb, C.K. Winkler, M. Tinzl, S.M. Glueck, Enzymatic conversion of CO2: From natural to artificial utilization. Chem. Rev., 123 (2023) 5702-5754.
[10] X. Zhao, S. Yang, S. Ebrahimiasl, S. Arshadi, A. Hosseinian, Synthesis of six-membered cyclic carbamates employing CO2 as building block: A review. J. CO2 Util., 33 (2019) 37-45.
[11] J. Luo, I. Larrosa, C− H carboxylation of aromatic compounds through CO2 fixation. ChemSusChem, 10 (2017) 3317-3332.
[12] S.R. Shah, N.J. Mazumdar, A. Centeno-Pedrazo, D. Deka, N. Artioli, H. Manyar, Recent advances in catalyst design for carboxylation using CO2 as the C1 feedstock. Catalysts, 13 (2023) 1489.
[13] S. Pradhan, S. Das, Recent Advances on the Carboxylations of C(sp3)–H Bonds Using CO2 as the Carbon Source. Synlett. 34 (2023) 1327-1342.
[14] S.S. Bharate, Carboxylic acid counterions in FDA-approved pharmaceutical salts. Pharm. Res., 38 (2021) 1307-1326.
[15] E. Bermejo, R. Carballo, A. Castineiras, A.B. Lago, Coordination of α-hydroxycarboxylic acids with first-row transition ions. Coord. Chem. Rev., 257 (2013) 2639-2651.
[16] (a) S. Sáez‐Orviz, I. Marcet, M. Rendueles, M. Díaz, The antimicrobial and bioactive properties of lactobionic acid. J. Sci. Food Agric., 102 (2022) 3495-3502; (b) T.O. Hester, G. Theilman, W. Green, R.O. Jones, Cyclandelate in the management of tinnitus: a randomized, placebo-controlled study. Otolaryngol. Head Neck Surg., 118 (1998) 329-332; (c) Y.E. Yarker, K.L. Goa, A. Fitton, Oxybutynin: a review of its pharmacodynamic and pharmacokinetic properties, and its therapeutic use in detrusor instability. Drugs Aging, 6 (1995) 243-262.
[17] K. Masada, S. Kusumoto, K. Nozaki, Reductive coupling of carbon dioxide and an aldehyde mediated by a copper (I) complex toward the synthesis of α-hydroxycarboxylic acids. Org. Lett., 22 (2020) 4922-4926.
[18] M. Chatterjee, A. Chatterjee, H. Kawanami, Production of lactic acid mediated by compressed carbon dioxide on heterogeneous Ni(ii) catalysts: a facile approach. Green Chem., 24 (2022) 6145-6155.
[19] G.M. Cao, X.L. Hu, L.L. Liao, S.S. Yan, L. Song, J.J. Chruma, L. Gong, D.G. Yu, Visible-light photoredox-catalyzed umpolung carboxylation of carbonyl compounds with CO2. Nat. Commun., 12 (2021) 3306.
[20] S. Okumura, Y. Uozumi, Photocatalytic carbinol cation/anion umpolung: Direct addition of aromatic aldehydes and ketones to carbon dioxide. Org. Lett., 23 (2021) 7194-7198.
[21] S. Bhatt, S. Saini, B.M. Abraham, A. Malik, S.L. Jain, Heterostructured Ti-MOF/g-C3N4 driven light assisted reductive carboxylation of aryl aldehydes with CO2 under ambient conditions. J. Catal., 417 (2023) 116-128.
[22] (a) M.C. Leech, A.D. Garcia, A. Petti, A.P. Dobbs, K. Lam, Organic electrosynthesis: from academia to industry. React. Chem. Eng., 5 (2020) 977-990; (b) L. Ma, X. Gao, X. Liu, X. Gu, B. Li, B. Mao, Z. Sun, W. Gao, X. Jia, J. Chen, Recent advances in organic electrosynthesis using heterogeneous catalysts modified electrodes. Chin Chem. Lett., 34 (2023) 107735.
[23] (a) H. Senboku, A. Katayama, Electrochemical carboxylation with carbon dioxide. Curr. Opin. Green Sustain. Chem., 3 (2017) 50-54; (b) S. Wang, T. Feng, Y. Wang, Y. Qiu, Recent Advances in Electrocarboxylation with CO2. Chem. Asian J., 17 (2022) 202200543; (c) X.F. Liu, K. Zhang, L. Tao, X.B. Lu, W.Z. Zhang, Recent advances in electrochemical carboxylation reactions using carbon dioxide. Green Chem. Eng., 3 (2022) 125-137.
[24] L. Muchez, D.E. De Vos, M. Kim, Sacrificial anode-free electrosynthesis of α-hydroxy acids via electrocatalytic coupling of carbon dioxide to aromatic alcohols. ACS Sustain. Chem. Eng., 7 (2019) 15860-15864.
[25] F. Boissou, S. Baranton, M. Tarighi, K.D.O. Vigier, C. Coutanceau, The potency of γ-valerolactone as bio-sourced polar aprotic organic medium for the electrocarboxlation of furfural by CO2. J. Electroanal. Chem., 848 (2019) 113257.
[26] K. Singh, H.S. Sohal, B. Singh, Synthesis of α-hydroxycarboxylic acids from various aldehydes and ketones by direct electrocarboxylation: a facile, efficient and atom economy protocol. Asian J. Chem., 33 (2021) 839-845.
[27] J. Seidler, A. Roth, L. Vieira, S.R. Waldvogel, Electrochemical CO2 utilization for the synthesis of α-hydroxy acids. ACS Sustain. Chem. Eng., 11 (2022) 390-398.
[28] M. Juhl, J.W. Lee, Umpolung reactivity of aldehydes toward carbon dioxide. Angew. Chem., Int. Ed. Engl., 57 (2018) 12318-12322.
Volume 7, Issue 2 - Serial Number 2
March and April 2024
Pages 148-158

  • Receive Date 19 December 2023
  • Revise Date 24 January 2024
  • Accept Date 24 January 2024